Section 24.2 Nucleophilic Catalysis 1001THE NOBEL PRIZE
Throughout this text, you have found biographi-
cal sketches that give you some information
about the men and women who created the science you are
studying. You have seen that many of these people are Nobel
Prize winners. The Nobel Prize is considered by many to be
the most coveted award a scientist can receive. The awards
were established by Alfred Bernhard Nobel (1833–1896).
The first prizes were awarded in 1901. Nobel was born in Stock-
holm, Sweden. When he was nine, he moved with his parents to
St. Petersburg, where his father manufactured the torpedoes and
submarine mines he had invented for the Russian government.
As a young man, Alfred did research on explosives in a factory
his father owned near Stockholm. In 1864, an explosion in the
factory killed his younger brother, causing Alfred to look for
ways to make it easier to handle and transport explosives. The
Swedish government would not allow the factory to be rebuilt
because of the many accidents that had occurred there. Nobel,
therefore, established an explosives factory in Germany, where,
in 1867, he discovered that if nitroglycerin were mixed with dia-
tomaceous earth, the mixture could be molded into sticks that
could not be set off without a detonating cap. Thus, Nobel in-
vented dynamite. He also invented blasting gelatin and smoke-
less powder. Although he was the inventor of explosives used by
the military, he was a strong supporter of peace movements.
The 355 patents Nobel held made him a wealthy man. He
never married, and when he died, his will stipulated that the
bulk of his estate ($9,200,000) be used to establish prizes to be
awarded to those who “have conferred the greatest benefit on
mankind.”He instructed that the money be invested and the in-
terest earned each year be divided into five equal portions “to
be awarded to the persons having made the most important
contributions in the fields of chemistry, physics, physiology
or medicine, literature, and to the one who had done the most or
the best work toward fostering fraternity among nations, theabolition of standing armies, and the holding and promotion of
peace congresses.”Nobel also stipulated that in awarding the
prizes, no consideration be given to the nationality of the candi-
date, that each prize be shared by no more than three persons,
and that no prize be awarded posthumously.
Nobel gave instructions that the prizes for chemistry and
physics were to be awarded by the Royal Swedish Academy of
Sciences, for physiology or medicine by the Karolinska Insti-
tute in Stockholm, for literature by the Swedish Academy, and
for peace by a five-person committee elected by the Norwegian
Parliament. The deliberations are secret, and the decisions can-
not be appealed. In 1969, the Swedish Central Bank established
a prize in economics in Nobel’s honor. The recipient of this
prize is selected by the Royal Swedish Academy of Sciences.
On December 10—the anniversary of Nobel’s death—the
prizes are awarded in Stockholm, except for the peace prize,
which is awarded in Oslo.Alfred Bernhard Nobel24.2 Nucleophilic Catalysis
A nucleophilic catalystincreases the rate of a reaction by acting as a nucleophile; it
forms an intermediate by forming a covalent bond with one of the reactants.
Nucleophilic catalysis, therefore, is also called covalent catalysis. A nucleophilic cat-
alyst increases the reaction rate by completely changing the mechanism of the reaction.
In the following reaction, iodide ion increases the rate of conversion of ethyl chlo-
ride into ethyl alcohol by acting as a nucleophilic catalyst:
To understand how iodide ion catalyzes this reaction, we need to look at the mecha-
nism of the reaction both with and without the catalyst. In the absence of iodide ion,
ethyl chloride is converted into ethyl alcohol in a one-step SN 2 reaction.
I−
CH 3 CH 2 Cl + HO H 2 O
− CH +
3 CH 2 OH Cl−a nucleophilic
catalystA nucleophilic catalyst forms an
intermediate by forming a covalent
bond with a reactant.